A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl CompoundsRobert E. RosenbergStudents teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones. Rosenberg, Robert E. J. Chem. Educ.2007, 84, 1474.

Addition Reactions |

Aldehydes / Ketones |

Esters |

Grignard Reagents |

IR Spectroscopy |

Oxidation / Reduction |

Reactions |

Student-Centered Learning

Oxidation of Aromatic Aldehydes Using OxoneRajani Gandhari, Padma P. Maddukuri, and Thottumkara K. VinodDescribes an eco-friendly procedure for the oxidation of aldehydes to carboxylic acids in water or a water-ethanol mixture using Oxone as the oxidant. The use of eco-friendly solvents, a non-toxic reagent, and the elimination of extraction solvents in the procedure demonstrate important green chemistry themes to students.Gandhari, Rajani; Maddukuri, Padma P.; Vinod, Thottumkara K. J. Chem. Educ.2007, 84, 852.

Ozonolysis Problems That Promote Student ReasoningRay A. Gross Jr.The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products.Gross, Ray A., Jr. J. Chem. Educ.2006, 83, 604.

A Microwave-Assisted Reduction of Cyclohexanone Using Solid-State-Supported Sodium BorohydrideLori L. White and Kevin W. KittredgeWe report a microwave-assisted reduction of cyclohexanone by sodium borohydride that is supported on SiO2. The reaction was completed in less than 3 minutes. Workup and analysis by GCMS, IR, and 1H NMR was possible in a two and half-hour laboratory session. This reduction was used successfully in a second-year organic chemistry laboratory. Students were exposed to a green chemistry reaction using solid-state-supported reactants in the absence of solvent. White, Lori L.; Kittredge, Kevin W. J. Chem. Educ.2005, 82, 1055.

Oxidation / Reduction |

Solid State Chemistry |

Green Chemistry |

Alcohols |

Aldehydes / Ketones

Following Microscale Organic Reactions Using FT-IREms-Wilson, JaniceThe progress of two microscale reactions, the reduction of cyclohexanone with sodium borohydride and the photochemical formation of benzopinacol, was monitored, qualitatively, using FT-IR.Ems-Wilson, Janice J. Chem. Educ.1996, 73, A171.

Microscale Lab |

Aldehydes / Ketones |

Photochemistry |

Oxidation / Reduction |

IR Spectroscopy

The Mechanism of NaBH4 Addition to Aldehydes: A Labeling ExperimentRolland K. Robinson and Karl De JesusIn order to determine the sources of hydrogens in NaBH4 reductions of aldehydes, a series of reductions were carried out using differentially deuterated reagents and solvents. Robinson, Rolland K.; De Jesus, Karl. J. Chem. Educ.1996, 73, 264.

The subjection of glutaraldehyde to the Tollens testHill, William D., Jr.Redox equations have been established for the Tollens test with respect to compounds containing two aldehyde groups such as glutaraldehyde.Hill, William D., Jr. J. Chem. Educ.1990, 67, 329.

Aldehydes / Ketones |

Oxidation / Reduction

Selective oxidation in the presence of a heterocycleBowles, K. Dean; Quincy, David A.; McKenna, John I.; Natale, N. R.The process of weighing the advantages and disadvantages of various oxidation methods are presented in this paper.Bowles, K. Dean; Quincy, David A.; McKenna, John I.; Natale, N. R. J. Chem. Educ.1986, 63, 358.

A phase transfer catalyzed permanganate oxidation: preparation of vanillin from isoeugenol acetateLampman, Gary M.; Sharpe, Steven D.There are several attractive features in this reaction sequence for the undergraduate laboratory. These include (1) use of a protecting acetate group, (2) use of a familiar "textbook" oxidant, potassium permanganate, (3) use of phase transfer catalyst, (4) preparing of an aldehyde, (5) short reaction period, and (6) the laboratory has a pleasant aroma.Lampman, Gary M.; Sharpe, Steven D. J. Chem. Educ.1983, 60, 503.